(E)-3-(tert-butyl)-2-hydroxy-5-(3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)benzaldehyde | 1616108-73-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(tert-butyl)-2-hydroxy-5-(3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)benzaldehyde
• CAS: 1616108-73-6
• 化学式: C₁₈H₁₈O₃S
• 分子量: 314.405
• InChiKey: MFTITKDPXQYMRA-VOTSOKGWSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  439.8±45.0 °C(predicted)
• 密度：
  1.227±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-氨基噻唑-4-甲酸乙酯 、 (E)-3-(tert-butyl)-2-hydroxy-5-(3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)benzaldehyde 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到ethyl 2-((E)-(3-(tert-butyl)-2-hydroxy-5-((E)-3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)benzylidene)amino)thiazole-4-carboxylate
  参考文献：
  名称：

  Novel Chalcone–Thiazole Hybrids as Potent Inhibitors of Drug Resistant Staphylococcus aureus

  摘要：

  A series of novel hybrids possessing chalcone and thiazole moieties were synthesized and evaluated for their antibacterial activities. In general this class of hybrids exhibited potency against Staphylococcus aureus, and in particular, compound 27 exhibited potent inhibitory activity with respect to other synthesized hybrids. Furthermore, the hemolytic and toxicity data demonstrated that the compound 27 was nonhemolytic and nontoxic to mammalian cells. The in vivo studies utilizing a S. aureus septicemia model demonstrated that compound 27 was as potent as vancomycin. The results of antibacterial activities underscore the potential of this scaffold that can be utilized for developing a new class of novel antibiotics.

  DOI：

  10.1021/acsmedchemlett.5b00169
• 作为产物：
  描述：

  2-叔丁基苯酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 (E)-3-(tert-butyl)-2-hydroxy-5-(3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)benzaldehyde
  参考文献：
  名称：

  吲哚-查尔酮基苯并吡喃类化合物的合成及生物评价作为有望的抗连接酶和抗增殖剂

  摘要：

  DNA复制和修复是复杂的过程，通过酶和蛋白质网络的协同作用来完成。DNA连接酶通过催化DNA链之间的缺口连接，在这些过程中起着至关重要的作用。与正常细胞相比，据报道在某些癌症中人类DNA连接酶I（hLigI）的水平升高。我们研究了抑制hLigI介导的DNA切口封闭活性，然后研究了基于吲哚-查尔酮的新型苯并吡喃化合物对癌细胞的抗增殖活性。与其他连接酶相比，一种称为化合物27的分子表现出对hLigI抑制的显着偏好，与正常细胞相比，对结肠癌（DLD-1）细胞的细胞毒性增强。机理研究表明，化合物27在连接过程中直接与hLigI相互作用，而与DNA底物不相互作用。这种新型有效的hLigI抑制剂对模拟实体瘤的DLD-1细胞的单层培养和3D培养均显示出显着抑制作用。它还影响了DLD-1细胞的迁移，表明其潜在的抗转移活性。因此，这种新颖的hLigI抑制剂可以作为抗癌药物开发的有希望的先导。

  DOI：

  10.1016/j.ejmech.2017.11.015

文献信息

• Synthesis and antifilarial activity of chalcone–thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi
  作者：Koneni V. Sashidhara、K. Bhaskara Rao、Vikas Kushwaha、Ram K. Modukuri、Richa Verma、P.K. Murthy

  DOI：10.1016/j.ejmech.2014.05.029

  日期：2014.6

  Here we report the synthesis of novel chalcone thiazole compounds and their antifilarial activity. The antifilarial properties of these hybrids were assessed against microfilariae as well as adult worms of Brugia malayi. Among all the synthesized compounds, only two compounds, namely 4g and 4n were identified to be promising in vitro. These active compounds were tested in B. malayi-jird (Meriones unguiculatus) and B. malayi-Mastomys coucha models. Compound 4n showed 100% embryostatic effect and 49% macrofilaricidal in jirds and M. coucha models, respectively. This study provides a new structural clue for the development of novel antifilarial lead molecules. (C) 2014 Elsevier Masson SAS. All rights reserved.